I knew a guy in the late 90s who checked himself into jail every winter. He just didn't have enough money to heat his home and buy food at the same time, and he was disabled and couldn't land a job in construction no more, so that's the only thing he found to stay alive.
When the snow started to come down, he'd go to our local minimart with a plastic gun. You know, like the really cheesy ones with a red cap at the muzzle, to make sure nobody would think it was real and gun him down my mistake, and to avoid getting a harsh sentence. He knew the store owner, since it was a small town and everybody knew each other.
He'd say hello, point the gun at him and gently say "Could you please call the police like last year?" The store owner used to try to talk him out of it, but he'd say "Don't force me to make it real because I don't wanna."
Then the sheriff would show up - they knew each other too of course - and he would try to convince him this wasn't a good idea. And the guy would say "Look, will you book me or not? Because if you don't, you'll come back next week to my place but with the coroner this time."
So the sheriff would book him. And the judge, who knew exactly why he was there at the trial, would sentence him to 5 months - time enough to get out in spring.
After I left town, I heard he kept doing that for many years, until he got tired of being poor and committed suicide.